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Windows Server Jobs in Chicago, IL (NOW HIRING)

IPsoft Inc.

Windows Administrator

Chicago, IL

$45 - $56.50/hr

Diagnose and remediate issues with Windows Server Infrastructure, and related roles and features, as well as other Microsoft and third-party Windows business infrastructure applications, while ...

blueStone

Server Administrator

Hoffman Estates, IL

The Server Administrator is responsible for the installation, configuration and maintenance of the organization's Windows Server operating systems and all related systems software. The Server ...

TEKsystems

Systems Engineer - Traveling

Chicago, IL

$50 - $60/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

The ideal candidate will have hands-on experience with Windows Server, VMware/Hyper-V virtualization, Active Directory administration, SQL Server backup and restore activities, and a solid ...

Kirkland & Ellis LLP

Server Engineer II

Chicago, IL · On-site

$116K - $144K/yr

  • Medical

  • Retirement

  • PTO

Server Operations & Support - Provide advanced administration and Level 2 support for global Windows and Linux environments; manage hypervisors including VMware vSphere, Nutanix Acropolis, and Hyper ...

Kirkland & Ellis LLP.

Server Engineer II

Chicago, IL · On-site

$116K - $144K/yr

  • Medical

  • Retirement

  • PTO

As a Server Engineer II, you'll play a key role on our global Server Operations team, supporting ... global Windows and Linux environments; manage hypervisors including VMware vSphere, Nutanix ...

TSIT Digital Technologies Inc

DC Ops Lead

Chicago, IL · On-site

Windows Server environments * Linux platforms (RHEL, CentOS, Ubuntu) * Ensure 24x7 availability, performance, and stability of compute services * Drive SLA adherence, uptime targets, and operational ...

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All JobsWindows Server JobsWindows Server Jobs in Chicago, IL

Windows Server information

See Chicago, IL salary details

$92.2K

$111.1K

$128.3K

How much do windows server jobs pay per year?

As of Aug 18, 2026, the average yearly pay for windows server in Chicago, IL is $111,065.00, according to ZipRecruiter salary data. Most workers in this role earn between $101,500.00 and $120,500.00 per year, depending on experience, location, and employer.

What is a Windows Server?

A Windows Server job involves managing, maintaining, and troubleshooting Microsoft's Windows Server operating systems in an IT environment. Professionals in this role configure servers, ensure security, handle updates, and support network infrastructure. They may also work with Active Directory, virtualization, and cloud integration to optimize system performance.

What are the typical day-to-day responsibilities of a Windows Server administrator?

As a Windows Server Administrator, your daily tasks often include monitoring server performance, applying updates and patches, managing user accounts through Active Directory, and resolving system issues to minimize downtime. You may also be responsible for backup operations, security checks, and supporting end-users or other IT staff with server-related concerns. Collaboration is common, as you'll frequently work alongside network administrators, cybersecurity professionals, and support teams to ensure seamless IT operations. These responsibilities require a proactive approach to system management and strong attention to detail. Developing your skills in this role can open up opportunities for advancement into senior administration or network management positions.

What are the key skills and qualifications needed to thrive in the Windows Server position, and why are they important?

To thrive as a Windows Server Administrator, you need a solid understanding of Windows Server operating systems, Active Directory, networking, and systems troubleshooting, often backed by a relevant degree or IT certifications. Familiarity with tools such as PowerShell, Hyper-V, and certifications like Microsoft Certified: Windows Server Fundamentals or MCSA are typically required. Strong problem-solving skills, effective communication, and the ability to work well under pressure are important soft skills for this role. These abilities are essential to ensure reliable system performance, rapid issue resolution, and successful collaboration within IT teams.

What are Windows Server roles?

Windows Server roles are specific functions or services that a Windows Server operating system can perform, such as Active Directory Domain Services, DHCP, DNS, File and Storage Services, and Web Server (IIS). These roles enable the server to provide various network and infrastructure services essential for enterprise environments and can be installed and managed through Server Manager or PowerShell. Understanding these roles helps IT professionals configure and optimize server environments effectively.

What can you do with a Windows Server?

A Windows Server administrator manages and maintains Windows Server environments, including configuring network services, managing user accounts, deploying applications, and ensuring security and system stability. They also handle tasks such as setting up Active Directory, virtualization with Hyper-V, and implementing backup and disaster recovery solutions.

What are the most commonly searched types of Windows Server jobs in Chicago, IL?

The most popular types of Windows Server jobs in Chicago, IL are:

What are popular job titles related to Windows Server jobs in Chicago, IL?

For Windows Server jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Windows Server jobs in Chicago, IL look for?

The top searched job categories for Windows Server jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Windows Server jobs?

Cities near Chicago, IL with the most Windows Server job openings:

Windows Server jobs near you
Infographic showing various Windows Server job openings in Chicago, IL as of August 2026, with employment types broken down into 75% Full Time, 20% Part Time, and 5% Contract. Highlights an 93% Physical, 3% Hybrid, and 4% Remote job distribution, with an average salary of $111,065 per year, or $53.4 per hour.

Windows Server Team Lead

CTC Lateral - Website & LinkedIn

Chicago, IL • Hybrid

Full-time

Re-posted 14 days ago

Job description

As a Windows Server Team Lead, you will work within Infrastructure to design, build, and operate scalable systems that support the business. Your focus will be on Windows server platforms, identity services, automation, and reliability engineering across onprem Windows environments and hybrid cloud integrations.

What You'll Do

  • Lead and develop a team of Windows Server engineers, setting priorities and focusing effort on highimpact reliability and platform initiatives.
  • Design and implement highperformance Windows Server solutions with a strong emphasis on availability, operational excellence, and latencysensitive trading workloads.
  • Drive automation and infrastructureascode practices to improve deployment consistency, reduce manual work, and scale operations.
  • Lead Active Directory modernization and hybrid identity initiatives, ensuring secure, reliable access across the firm.
  • Partner closely with Security, Infrastructure, and Development teams to plan and deliver changes safely and predictably.
  • Improve incident response through clear leadership during events, root cause analysis, and durable preventative followups.
  • Contribute to resource management, forecasting requirements, and enhancing performance to support peak market activity.
  • Produce and maintain documentation (runbooks, diagrams, postincident reviews) to support knowledge sharing and continuous improvement.
  • Participate in an oncall rotation and provide leadership during critical incidents as needed.

What We're Looking For

  • Good interpersonal skills with the ability to lead, mentor, and collaborate across technical teams.
  • A pragmatic approach that balances fast delivery with longterm maintainability and operational excellence.
  • Ability to triage and resolve issues endtoend, including clear ownership of root cause and prevention.
  • 8+ years of handson Windows Server administration experience in critical, highavailability environments.
  • Deep expertise in Windows Server, Active Directory, Group Policy, DNS, DHCP, and Failover Clustering, including performance tuning and resolving complex challenges.
  • Proven leadership experience running infrastructure teams (or acting as a senior technical lead), with a record of developing engineers and driving standards.
  • Strong PowerShell scripting/automation skills; experience with infrastructureascode tools and/or configuration management (or demonstrated willingness to adopt and lead these efforts).
  • Willingness to participate in an oncall rotation and lead through highseverity incidents.
  • Meticulous attention to procedure, change management, and meeting service expectations.

Nice to Haves

  • Experience with enterprise platforms such as SCCM/MECM, endpoint/server monitoring, backup systems, and/or load balancers.
  • Familiarity with ITIL concepts, operational workflows, project management, and DevOps/CI/CD practices.
  • Experience supporting financial services infrastructure, trading systems, or market data platforms.
  • Exposure to modern deployment approaches (e.g., containerization, orchestration).

Work Location and Collaboration

This role is based in Chicago, working closely with Infrastructure, Security, Networking, and Development teams for highbandwidth collaboration. We value facetoface teamwork and pragmatic flexibility.

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